Hydrogen Peroxide → HCID 19753535, compound

HRID 483706Notes

Reaction equation

HRID 483706 reaction equation
[CH3:1][O:2][C:3]([CH3:14])(C)[CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][C:8](=[O:12])[CH2:7]1.[CH:15]([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].[OH-].[Na+].OO>O1CCCC1>[CH3:1][O:2][CH:3]([CH3:14])[CH2:4][CH:5]([CH3:15])[CH:6]1[CH2:11][CH2:10][CH2:9][CH:8]([OH:12])[CH2:7]1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 3611392Lithium tri-s-butylborohydrideHCID 14794002HCID 14794002, compound

Product 1

HCID 19753535HCID 19753535, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-(3-methoxy-3-methylbut-1-yl)cyclohexanone (1.4 g. 0.0051 mol) was dissolved in tetrahydrofuran (10 mL) and cooled to -78~C. under a nitrogen atmosphere with stirring. A solution of lithium tri-sec-butylborohydride (6.1 mL of a 1M solution of tetrahydrofuran, 0.0061 mol) was added. The mixture was allowed to come to 20~C. over 16 hours and 10% NaOH (aq, 4.0 mL) was added, followed by 30% hydrogen peroxide (aq, 4.0 mL). The mixture was extracted with hexane. The extracts were dried (Na2SO4) and concentrated to the residue which was purified by bulb to bulb distillation (air bath temp 175~C., 0.1 mm Hg) to yield 3-(3-methoxy-methylbut-1-yl)cyclohexanol as a mixture of diastereoisomers in the ratio of 94:6 (0.7 g). NMR(CDCl3)δ 1.1(s,6H), 1.2-1.8(m,13H), 3.2(s,3H), 4.1(brs,1H). IR (neat) 3410, 2990, 2960, 2870, 1460, 1370, 1110, 1090, 980 cm-1. MS (m/e) 43, 73, 109, 124, 143, 181, 201, 214.

Workup

  1. temperaturecooled to -78~C
  2. extractionThe mixture was extracted with hexane
  3. dry with materialThe extracts were dried (Na2SO4)
  4. concentrationconcentrated to the residue which
  5. distillationwas purified by bulb to bulb distillation (air bath temp 175~C., 0.1 mm Hg)

Sources & evidence

ORD record
ord-75c8f79c31e84c02ba41d4431360acc2
Source dataset
uspto-grants-1993_07
Patent number
US05225608

Reaction notes

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